Deep Sea Driver

Georgia-based trucker Daniel Whitchurch will use time away from behind the wheel to take his 30-foot cutter out into open waters.

Daniel Whitchurch likes rough water.

When the wind howls, he’s ready to go, eager to shove off and take on weather that few sailors would want to challenge.

The 47-year-old driver, who says his approach to sailing weather is “it’s OK if I can get the boat away from the dock,” took his wife and daughter sailing in the Seattle area the day after Christmas. “The wind was about 35 knots, and it was rough and it was snowing. We all wore wet suits under our clothes to stay warm and had ski masks on. The Coast Guard thought we’d only come out to help look for some lost kayakers instead of being a family out for a day’s sailing.”

And it was on another 35-knot day in the middle of a cold January that Whitchurch took a 40-foot sailboat out to sea and managed to surf it along the wave tops at 11 knots (that doesn’t sounds like much, but imagine a Class 8 tractor going faster than you ever thought it could go). “We were flying,” he says. “What a wild ride that was.”

“To me,” he says, “sailing feels like a combination of the feelings you get when you ride a Harley-Davidson and the feeling you get when you jump out of a plane.”

A 28-year over-the-road veteran with more than 3 million miles under his belt, Whitchurch and Debra, his wife of 26 years, drive team for Kennesaw Transportation, piloting a 2005 Pete 387. Whitchurch, based in Cartersville, Ga., learned to sail about the same time he learned to drive a big truck – at age 12.

He was born in northern California and lived right on Humbolt Bay, the deep-water port where he first learned to sail.

“I’ve been sailing and loving it all my life,” he says.

His family owned hay and logging trucks since 1939 until about four years ago.

“My grandfather would have us all learning and driving the logging trucks, and he’d say once you could handle a logging truck you could work the hay trucks,” Whitchurch says.

Whitchurch left home and ended up in the Marine Corps, where he continued sailing. He’d come back home over the holiday season and fill in for drivers taking time off from the company business to be with their families.

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It was in his earliest days of sailing that Whitchurch might have picked up his love of rough water.

“I learned a lot off Cape Mendocino just south of here,” he says. “It’s the westernmost point of California, and it’s kind of our Cape Horn. It can be treacherous in those waters. Two different currents collide, and the weather and the water on one side of her can be totally different from the other. I’m always prepared for any kind of weather going around her. Sometimes it’s nothing, but I learned to get ready for her moods because they change so quickly.”

These days one of Whitchurch’s favorite places to sail is in and around the San Juan Islands in the northern reaches of Puget Sound, about 80 miles north of Seattle. There are more than 170 islands in the group, some large, some tiny and some accessible only by sailboats.

“I was in Inati Bay up in the San Juans one time, and it must have been about 2 in the morning,” he says. “I was out on the stern just watching and listening. Next thing there’s an orca (the famous black and white killer whales) right behind the boat, only a few feet from me, and it kind of rolled over and he was looking at me, almost like he was trying to communicate with me, and he had this mischievous little grin.

“I just love being out there and being so close to the wildlife in those pristine conditions. You can see porpoises and orcas and Minke whales and bald eagles all day long.”

Whitchurch also enjoys sailing the Caribbean, but he says those waters have more of a party atmosphere and he’d rather sail in the more spiritually satisfying atmosphere of Puget Sound. “There’s not so much garbage in the water, there are no personal water craft in most places up there, and there’s more little pubs and arts and crafts shop and not so many rhumba bands,” he says.

These days Whitchurch’s sailing craft is a Kenner Privateer docked in Savannah, Ga. “It’s a 30-foot cutter rig, and she’s ocean capable so we can take her down to the Bahamas or Bermuda, Key West or Grenada.” When he sails in the San Juans these days, he’s likely to charter a boat and maybe take family and friends on cruises, or occasionally act as captain for a charter boat company. Whitchurch says he’s licensed to captain “anything up to 50 feet in any conditions.”

He plans his sailing vacations months in advance. “Deb and I will run three to four weeks in the truck, then come back and take eight days off, maybe five sailing and three at home,” Whitchurch says. “I let Kennesaw know what I’m planning, and they work with me to make it happen. But I’d like to sail more than I do; that’s one of the reasons I wrote the book.”

The “book” is an action thriller called The Pied Piper Project – Russia’s Child, a tense drama pitting the CIA and KGB against each other with a maverick hero at the center of the action.

“My plan is for us to sail around the world. I could leave the boat somewhere and come back and do some driving if I had to, then go back,” Whitchurch says. “I figure it would take about three years. Writing books could help me pay for it, and maybe I wouldn’t have to come home and drive so much. I’d like to be sitting on the boat in the sun writing more books. I’ve spent 28 years putting chains on in ice and snow, and my body is telling me it’s time for the sun.”

Whitchurch has traveled across the world before but hasn’t yet sailed the whole way round.

“My dad bought a 41-foot boat a couple of years ago, and I knew he wanted to take it around the world. But it hasn’t happened,” he says. “I took every course I needed to be certified to sail with him, but not yet. But he’s a fine sailor. He told me once ‘I’d rather be on a sailboat on 40-foot waves than in a truck on two inches of ice.’ I agree with that 100 percent now.

“And I sailed with a guy who was sailing from America to Bermuda then on to the Azores and into Gibraltar and the Mediterranean. I got off in Bermuda, had to come back and go driving.”

Whitchurch also took off for the Orient on board a giant ship. “I was talking to a guy in Stockton, Calif., and he sailed on a cargo ship. He told me that they had cabins for passengers, nothing fancy, but real cheap. For $350 I sailed to Thailand and then flew back.

“I also sailed out from the West Coast to Hawaii and on to Christmas Island and down into the South Pacific and the Cook Islands. But then I flew home again. Next time, maybe Deb and me, we don’t stop, we just keep on sailing.”

Daniel and Debra Whitchurch formed a driving team seven years ago. “When our kids were pretty much grown, Deb came out on the road with me,” Whitchurch says. “I was running coast to coast and not getting home enough. She wanted to get on the road, so we teamed up and went to driving for Kennesaw, and they’re one of the best outfits I’ve ever worked for.”

Truck drivers make natural deep-water sailors, Whitchurch says.

There’s something about trucking that matches the skills and the mindset you need for blue-water sailing, according to Whitchurch. For example, the knots a flatbedder must know are the same as nautical knots. “There’s even a nautical knot called the Trucker’s Knot,” he says. “But it’s not just tying off ropes, its being behind the wheel.

“I was coming into a dock and clear customs on the way back from Victoria, Canada, in some heavy wind and seas, and a 50-foot power boat trying to get into the same dock just crunched right into the dock,” Whitchurch says. “After I tied up, the customs guy looks at my ID and sees it’s a CDL. ‘I knew it,’ he said, ‘truckers make the best sailors.’ And that’s not the only time I’ve heard that.”

Controlling a boat on a wave is similar to guiding a truck on ice, Whitchurch says.

“You can’t just stop and get off. Your mindset has to change, and you have to handle it, to feel the vehicle and know what she can do and how you can make her do it,” he says. “Good truckers spend so many hours behind the wheel they get to drive by ‘feel,’ and that’s how you handle a boat. You feel her weight and movement and know the best ways to maneuver. There’s also a sense of independence and freedom out there on the ocean that is similar to being on the road crossing the country.”

You can buy Whitchurch’s thriller on the Web at, or

Modern cattle drives give you the real-life experience of trailing a herd

Years ago, before cattle got to market via tractor-trailer, they walked.

Truckers are like cowboys – fiercely independent, rugged and refusing to be tamed or straightjacketed by the mainstream, the last of the truly American pioneer types. So why not visit a place where you can be cowboys?

Cattle drives still go on, and vacationing adventurers can be part of them at ranches specially set up to let you make those little doggies get along. Think of Billy Crystal in the movie City Slickers. Or for more reality, think Robert Duvall and Tommy Lee Jones in Lonesome Dove.

Most of these ranches are run by real cowboys who know and love their land and their work, although the inevitable hand of corporate ownership means the occasional boss might be a suit-wearer in Manhattan. Costs can range from around $100 a day to $2,000 a week. And if you find the right ranch, you’re doing real, satisfying work without a diesel, a phone, a television set or an air-conditioning unit in sight.

After the Civil War, cattle drives became common in the West. The newly peaceful country wanted beef, especially the big eastern cities, and there was a lot of it in Texas and the Southwest. But cattle were a long way from the rail lines that could carry them to the country’s beef-hungry big cities. Trails were developed to run cattle up to Kansas and the railhead, a journey of 1,000 miles or more that could take four dangerous months.

The men who drove the cattle were tough, especially the main man, the trail boss. For herds of several thousand cattle there could be as many as 50 cowboys and the associated cooks, horse wranglers and scouts. Amazingly, the average cowboy wasn’t even 18 years old, facing a life of 12-hour days in the saddle; night watches trying to keep the herd settled and safe from predators and rustlers; basic biscuit-bacon-beans-and-coffee diets; and a bed on the ground, rain or shine.

But when the herd reached the railhead, it was a wild scene. That’s when the cowboys got paid (a little like drivers, getting their money only when the cargo is safely delivered). Finally in a town and with no work, the cowboys made places like Dodge City and Wichita some of America’s original “sin cities,” with gambling, women and liquor freely for sale. But once the effect of the celebration wore off, there was only one way back to Texas or Arizona – the same way they had come. “Saddle up, boys, we’re riding home!”

But then the railroads reached down into Texas, New Mexico and Arizona, and after that came the tractor-trailer. The American cattle didn’t walk to market anymore.

Today’s drives are not as primitive as the old ones, but a really good ranch drive will let you share something of the life of those old trail cowboys. Good cattle-driving ranches today aren’t too fancy; there’s just you, horses and cows, so luxury is a rare commodity. Here are just three examples to whet your appetite and help you start looking for your ranch.

The five-day Montana Cattle Drive ( happens twice a year, in June and August. Cattle are driven in June from pasture on the floor of the Missouri River valley up into grazing land in the Big Belt mountains. The drive’s trail boss John Flynn says the drives are essential work for the full-time wranglers and the guests. Four or five guests are teamed with a wrangler to work a certain part of the pasture, gathering the cattle into a herd.

“Then when we move, we want the herd to string out, so a team may start with 20-25 head, and then another team will follow a little later so that we create a string of cattle,” Flynn says.

“In June you’re working with cows and calves, so a lot is happening. The cows know they are going to new grazing, so they’re looking up the trail. The calves remember the last time they sucked their mothers was back down the trail. Then sometimes a cow will stop to try and find a calf, so there’s a lot of stuff going on.”

But the city slickers enjoy the hard work, Flynn says. “I think they especially like doing something they know has to be done, and if they didn’t do it someone else would,” he says. “It’s a feeling of being useful.”

The TX Ranch in Lovell, Wyo., ( is another drive that’s not a vacation. “We’re all about moving the cattle along the base of the mountains,” says the ranch’s owner Loretta Tillet. “We’re not a dude ranch; we’re a no-frills working ranch. Evenings are spent around a campfire and nights in canvas-walled tents with a wood stove. We’re the real McCoy.

“We’ve thought of changing things, but guests keep coming back saying they want it to stay the same. They come and ride all day and work cattle. New guests find out they are working like old-fashioned cowboys, and they like that. It’s what they want.”

There’s also the 10-day Long Valley Cattle Drive ( in the fall. This is also the real deal, the annual move of cows from the high-country summer pastures near Bryce Canyon, Utah, to the winter range on the north rim of the Grand Canyon, run by the Heaton family, which has run cattle in this country since it was first settled.

“In the spring the cows have their calves so they are hauled up into Utah, but in the fall the cows are trail-driven back,” says Allida Heaton. “There’s usually about 800 cows and maybe eight to 10 people driving them. It’s roughing it, sleeping bags and tents, but we feed ’em good, and our people get something special.

“It’s an experience of what cattle driving is really like.”

The Business Manual for Owner-Operators
Overdrive editors and ATBS present the industry’s best manual for prospective and committed owner-operators. You’ll find exceptional depth on many issues in the 2022 edition of Partners in Business.
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